Production of ethyl benzene



' Patented Apr.3,1945 y 2,373,030 I PRODUCTION oFn'rnYL BENZENE PATENT OFFICE Charles N. Kimberlin; Jr Baton Rout r. as-

signer to Standard Oil-Development Company. a corporation oi Delaware No Drawing. Application July 12, 1941, Serial No. 402,191

scmms. (or. 260-611) The present invention is concerned.with the production or ethyl benzene. The invention is more particularly concerned with an improved catalyst for utilization in a reaction involving A satisfactory operating temperature is about 160 F. The mole ratio of the ethylene feed to benzene feed passed to the reaction zone likewise may vary considerably. In general, an appreethylene and benzene. In accordance with the ciable excess of benzene'over the stoichiometric P nt invention,-benzene and ethylene are reacted employing a catalyst comprising a noninetallic halide and a Friedel-Crafts type catalyst. It is known in the art to produce mono-ethyl amount needed is employed. I have found that approximately 0.2 to 0.4 mole of ethylene per 1.0 ,mole of benzene is satisfactory. It is preferred that the hydrogen chloride be recovered from benzene by reacting benzene and ethylene under the reaction product and recycled to the reaction suitable temperature and pressure conditions.

r These reactions are generally conducted at a temperature range from about 120 F. to about 250 F. Catalysts generally employed are conventional Friedel-Crafts type catalysts such as the various metallic halides, as for example aluminum chloride, zinc chloride, and iron chloride. In these reactions, certain difiiculties are encountered. For instance, in the production of mono-ethyl benzene, a relatively high percentage of poly- .ethyl benzenes are produced, as well as other reaction products. Furthermore, the yield of mono-ethyl benzene per unit weight of catalyst is relatively low. I have now discovered a process whereby a maximum yield of mono-ethyl benzene may be secured with a minimum consumption of catalyst. In accordance with my invention the reaction is conducted. in .the presence of a catalyst comprising aFriedel-Crafts type catalyst and a suitable non-metallic halide.

The Friedel-Crafts type catalyst may comprise any conventional catalyst of this. class, such as the various metallic halides as, for example, zinc chloride and iron chloride. I, however, prefer touse aluminum chloride in my process. non-metallic halide which I use in conjunction with the aluminum chloride preferably comprises hydrogen chloride, however other substances are satisfactory such as the various alkyl halides as,

The 35 311 zone. The reaction products may be treatedto separate the desired mono-ethyl benzene as well as di-ethyl benzene and higher boiling ethylene products.

J, In order to further illustrate my invention, the

following examples are given which should not be construed as limiting the same inany manner whatsoever:

Example 1.A number .of operations were conducted in which 0.3 mole of ethylene was treated with 1.0 mole of benzene at a temperature of 160 F. The catalyst employed in the various operations consisted of aluminum chloride and various concentrations of, hydrogen chloride. The

results of these operations were as follows:

Mole percent Yi 1d oih drogen e n chloride gffi Operation fi gggg benzene per that; vo me o ethylene chloride From the above it is apparent thatan apprefor example, ethyl chloride, carbon tetra-chloride, Mable increase in yield per \unit of ta lyst is and chloroform.

The amount of non-metallic halide employed in conjunction with the Friedel-Crafts catalyst may vary considerably, depending upon various operating conditions and the particular Friedel- Crafts catalyst employed. For example, when employing hydrogen chloride in conjunction witm aluminum chloride the amount of hydrogen chloride may vary from 3% to 100%, based upon the volume of ethylene feed. However, in general, I

secured in accordance with my invention.

Example 2.-In an operation conducted under conditions described with respect to Example 1,

' 10% of ethyl chloride was employed based upon the volume of ethylene feed. The results of this operation were as follows:

Mole percent of ethyl gfiggg chligride ethyl emp eye Operation based upon Wig-{211113 grer a uminum vo ume o ethylene chloride 1 1 0 a o 2 1o 1 0 From the above it is apparent that unexpected desirable results are secured in accordance with the range from about 140? F. to about 200 F. my process.

, What 1 claim as new and wish to protect by Letters Patent are 1. Process for the production of. mono-ethyl benzene which comprises reacting ethylene and benzene in the presence 01' a catalyst comprising an aluminum halide and a hydrogen halide, the amount of hydrogen halide being in the range from about 20 to about 100 mole per cent based upon the ethylene iced, separating. the reaction product, recovering the hydrogen halide and recycling the same.

2. Process for the production oi'mono-ethyl benzene which comprises reacting ethylene and benzene in the presence of an aluminum chloride catalyst and a non-metallic chloride promoter which yields hydrogen chloride under the conditions oi the reaction, the amount of said promoter being in the range from about 20 to about 100 male per cent'based upon the ethylene feed.

3. Process for the production of mono-ethyl benzene which comprises reacting ethylene and benzene in the presence of a catalyst consisting oi aluminum chloride and hydrogen chloride at a temperatureflin the range from about 140 F. to 200 E, the amount of hydrogen chloride being in the range from about 20 to about 100 mole per cent based upon-the ethylene feed.

CHARLES N. KIMBERLIN, JR. 

